Non-leaching surface-active film compositions for microbial adhesion prevention

A medical device for introduction into a human or animal body, comprising an antimicrobial coating on at least one surface of said device, said antimicrobial coating comprising:

• a polymeric matrix which comprises a polyurethane component;
• and
• at least one long chain surfactant chemically bonded to said polyurethane component, said surfactant projecting away from the surface of said antimicrobial coating and having sufficient length to protrude through organic debris deposited over time on the surface of said antimicrobial coating as a result of being introduced into a human or animal body, and
• wherein said surfactant is non-leaching and is capable of penetrating cell walls of microbial organisms and preventing microbial colonization over the surface of said antimicrobial coating.

A curable antimicrobial coating composition comprising:

• (a) at least one polyurethane prepolymer present in an amount from about 0.01% to about 20% based on the weight of the composition;
• (b) at least one carrier solvent capable of at least partially dissolving said polyurethane prepolymer, present in an amount from about 99.89% to about 75% based on the weight of the composition;
• (c) a hydrophilic component comprising a hydrophilic organic monomer, oligomer, prepolymer, polymer or copolymer derived from vinyl alcohol, N-vinylpyrrolidone, N-vinyl lactam, acrylamide, amide, styrenesulfonic acid, combination of vinylbutyral and N-vinylpyrrolidone, hydroxyethyl methacrylate, acrylic acid, vinylmethyl ether, vinylpyridylium halide, methyl cellulose, ethyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxymethyl ethyl cellulose, hydroxypropylmethyl cellulose, cellulose acetate, cellulose nitrate, starch, gelatin, albumin, casein, gum, alginate, hydroxyethyl(meth)acrylate, hydroxypropyl (meth)acrylate, ethylene glycol (meth)acrylates (e.g. triethylene glycol (meth)acrylate) and meth)acrylamide), N-alkyl(meth) acrylamides (e.g. N-methyl(meth)acrylamide and N-hexyl(meth)acrylamide), N,N-dialkyl(meth)acrylamides (e.g. N,N-dimethyl(meth)acrylamide and poly-N,N-dipropyl(meth)acrylamide), N-hydroxyalkyl (meth)acrylamide polymers, such as poly-N-methylol (meth)acrylamide and poly-N-hydroxy ethyl(meth)acrylamide, and N,N-dihydroxyalkyl(meth)acrylamide polymers, such as poly-N,N-dihydroxyethyl (meth)acrylamide, ether polyols, polyethylene oxide, polypropylene oxide, and poly(vinyl ether), alkylvinyl sulfones, alkylvinylsulfone-acrylates or a combination thereof, present in an amount from about 0.01 to about 40% based on the weight of the composition;
• and
• (d) at least one quaternary ammonium compound present in an amount from about 0.01% to about 5% based on the weight of the composition and having the following formula:
• wherein:
• L represents a hydrocarbon group which comprises at least one functional group capable of forming a chemical bond with said polyurethane prepolymer, upon curing of said coating composition by evaporation of said carrier solvent, and having sufficient length to allow said at least one quaternary ammonium compound to protrude through and beyond organic debris deposited over time on the surface of said cured coating composition, wherein said functional group is capable of reacting with the polyurethane prepolymer directly or with a crosslinker that is capable of crosslinking the quaternary ammonium compound with the polyurethane prepolymer upon evaporation of said carrier solvent;
• and
• at least one of R1, R2 and R3 represents a hydrocarbon group which is capable of penetrating cell walls of a microbial organism and killing said organism.

A non-leaching antimicrobial solid surface coating comprising a solid polymeric matrix covalently bound to an antimicrobial compound having the following formula:

• wherein:
• the polymeric matrix comprises a cured polyurethane;
• X represents —O—, —S—, —CO—, —COO—, —NH—CO—, or —NH—;
• L represents a chain extending, multifunctional linker, having a chain length sufficient to extend N equal to or beyond any proteinacious debris that builds up on the coating surface;
• N represents nitrogen or phosphor;
• and
• R1, R2 and R3 independently represent carbon chains, in which at least one R group has sufficient length to penetrate and destroy microbial cell walls, resulting in death of the cell.

A curable coating composition comprising:

• a polymeric matrix which comprises at least one polyurethane prepolymer;
• a carrier solvent;
• at least one long chain cationic surfactant compound comprising a functional group capable of forming a chemical bond with said polyurethane prepolymer upon evaporating said carrier solvent and drying or curing of said composition, said functional group selected from the group consisting of an amine, thiol, carboxyl, aldehyde, hydroxyl and combinations thereof;
• and
• at least one hydrophilic organic monomer, oligomer, prepolymer, polymer or copolymer derived from vinyl alcohol, N-vinylpyrrolidone, N-vinyl lactam, acrylamide, amide, styrenesulfonic acid, combination of vinylbutyral and N-vinylpyrrolidone, hydroxyethyl methacrylate, acrylic acid, vinylmethyl ether, vinylpyridylium halide, methyl cellulose, ethyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxymethyl ethyl cellulose, hydroxypropylmethyl cellulose, cellulose acetate, cellulose nitrate, starch, gelatin, albumin, casein, gum, alginate, hydroxyethyl(meth)acrylate, hydroxypropyl (meth)acrylate, ethylene glycol (meth)acrylates (e.g. triethylene glycol (meth)acrylate) and meth)acrylamide), N-alkyl(meth) acrylamides (e.g. N-methyl (meth)acrylamide and N-hexyl(meth)acrylamide), N,N-dialkyl(meth)acrylamides (e.g. N,N-dimethyl(meth)acrylamide and poly-N,N-dipropyl(meth)acrylamide), N-hydroxyalkyl (meth)acrylamide polymers, such as poly-N-methylol (meth)acrylamide and poly-N-hydroxy ethyl(meth)acrylamide, and N,N-dihydroxyalkyl (meth)acrylamide polymers, such as poly-N,N-dihydroxyethyl(meth)acrylamide, ether polyols, polyethylene oxide, polypropylene oxide, and poly(vinyl ether), alkylvinyl sulfones, alkylvinylsulfone-acrylates or a combination thereof;
• wherein said long chain cationic surfactant compound is non-leaching upon drying or curing said composition and has sufficient length to protrude through and beyond organic debris deposited over time on the surface of said cured composition;
• and
• wherein said cured composition exhibits reduced blood coagulation of blood in contact with said cured coating compared to a similar coating without said at least one long chain cationic surfactant compound.